Azo dye.



" 1m TED STATES PATEN F CE" KURT IDESAMARI, OSCAR G'O'NTHER, AND HUGO SCHWEITZER, OF, ELBERFELD, AND

ARTHUR ZART, 'VOHWINKEL, GERMANY, ASSIGNORS TO FARBENFABRIKEN VORM. FRIEDR. BAYER & (30., 0F ELBERFELD, GERMANY, A CORPORATION OF GER- I the German Empire, have invented new and useful Im rovements in Azo Dye, ofwhich the-followlng is a. specification.

The present invention relates to the manufacture and production of new azo dyestufis'capable of dyeing unmordanted cotton in from yellow to orange to brownred Shades which on being developed on the fiber become fast to washing.

The process for their production consists in converting into urea compounds the ami noazo compounds which are obtained by combining with suitable aromatic amins,

' and dyes cotton in orange shades/which such as orthoor meta-toluidin, para-xylidin,

cresidin; diazotized' 'aminonaphthol compounds, such as aminonaphthols, their sulfonic acids and derivatives 6. g. aminobenzoylaminonaphthol sulfonic acids, aminophenyloxynaphthimidazol sulfonic acids, which are substituted in the amino group by substituents containing a heteronuclear amino group capable of being diazotized. The urea compounds are produced in the usual Way by treatment with phosgene.

after being developed with diazotized paranitranilin yield a purej clear red-brown of excellent fastness to light and to washing, and capable of being discharged to apure white.

Patented Feb. 4, 1913.

A20 DYE.

1,052,135 specification of Letters Patent. No Drawing.

Applieation filed July 27, 1911. Serial No. 640,779. i

acid an aminonaphthol compoundand an urea of a diainin is obtained, which is split up into carbonic acid and a diamin.

In order to illustrate the new process more fully the following example is given, the parts being by weight:239' parts of l-amino-6-naphthol-3-sulfonic acid are diazotized with 69'parts of sodium nitrite and hydrochloric acid and the diazo compoundis combined in a very slightlyfhydrochloric acid solution with 187.5 parts of cresidin hydrochlorid. The monoazo dyestuffis isolated from the hydrochloric acid solution and is dissolved in water containing an excess of sodium carbonate. Into this solution phosgene is passed through the solution, which has to be-kept alkaline during this process and .ata moderate temperature of about 40 C. until the dyestufi is completely It is in the shape o f its alkaline salta dark I 7 powder easily soluble in wate'r with a yellow color and in concentrated sulfuric; acid with a blue violet color; yielding upon reduction with stannous chlorid and .hydrochloric acid resume l.6-sminonaphthol-dsulfoniz: acid and the symmetrical urea of 3.6-dieminocresolethylether CHa El e I diezotized pers-nitranilin are of excellent lastness to washing and to light and are cupuble of being discharged to a, pure white, substantially as described.

2. The new 'dyestufi's or? general lorinulu:

11-h?N-R--NH-GO-NH-Ri-N -NK1, Where it and R are eromutic radicals, and X and K are the radicals of naphthol sulfonic acids unsubstituted by amino groups, which are after bein dried and pulverized dark powders solub e in water generally with a yellow color and soluble in concentrated sult'onic acid with u reddish to violet color; yielding upon reduction with stunnous chlorid and hydrochloric acid a monowhich is utter being dried and pulverized a dork powder eesilysoluble in water with a yellow color and in concentrated sulfuric acid with e blue violet color; yielding u on reduction with stannous chlorid and hyrochloric acid l,6-eminonephthol-3-sulfonic acid-end the sminetricsl ures oil 3.6-dithe 7 following aminocresolethyether which is further decomposed into 3.6-dieminopurecresolethylether and carbonic acid; dyeing cotton in orange shades whichlefter being developed with diezotizcd pure-nitrenilin yield a ure clear red-brown or excellent fustness to ight uminonsphthol compound and an uree of s diamin; and dyeing-unmordanted cotton in from yellow to orange to brown-red shades, substantially as described.

3. The new dyestuds of the following general formula:

x-umu-s-un-cowa er-N nce,

where R and R are aroma-tic radicals and 3i and X are the radicals of ii-nsphthol- 3-sulionic acid, which are oft-er being dried and pulverized dark powders soluble in water generally with a yellow color and soluble in concentrated sulfuric acid with s reddish to violet color; yielding upon reduct-ion with ste'nnous' chlorid end hydrochloric acid 1-amino-tl-naphthol-3-sulfonic cold and en urea of e, diamin; end dyeing unmordanted cotton in from yellow 'to orange to brown-red shades, substantially as described.

- 4t. lhe new dyestutls of the following general formula:

where R und'lll are aromatic radicals of the benzene series and K and X are the radicals of ony-nophthalenes unsubstituted by amino groups, which are after being dried and pulverized dark powders soluble in. water generally with a yellow color and soluble in concentrated sulfuric acid with a reddish to violet color; yielding upon reduction with stannous chlorid and hydrochloric acid an aminonuphthol compound and an urea of s, diemin; and dyeing unniordanted cotton in from yellow to orange to brown-red shades, substantially as described.

5. The new dyestufi having most probably the formula: 1

soiu k/ v ou and capable of being discharged to or pure white, substantially we described lln testimony whereoll we hove hereunto set our hands in the presence of two subscribing witnesses.

KURT ,DESill /IARK. {no} 'osoen erlu'rrurrt. 1 e] HUGU SCHVVElllZER, [new] ART ZART, [is] Witnesses:

Archer l News, Bnonimrm, 

